4-Hydrazino-5,6-diphenyl-2-(trifluoromethyl)pyrimidine → 5-amino-1-[5,6-diphenyl-2-(trifluoromethyl)pyrimidin-4-yl]-3-(methylthio)-N-phenyl-1H-pyrazole-4-carboxamide

HRID 72687Notes

Reaction equation

HRID 72687 reaction equation
[NH:1]([C:3]1[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:6]=[C:5]([C:21]([F:24])([F:23])[F:22])[N:4]=1)[NH2:2].[C:25]([C:27](=[C:37](SC)[S:38][CH3:39])[C:28]([NH:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:29])#[N:26]>CO>[NH2:26][C:25]1[N:1]([C:3]2[C:8]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)=[C:7]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:6]=[C:5]([C:21]([F:24])([F:23])[F:22])[N:4]=2)[N:2]=[C:37]([S:38][CH3:39])[C:27]=1[C:28]([NH:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:29]

Participants

4

Reactant 2

HCID 100195084-Hydrazino-5,6-diphenyl-2-(trifluoromethyl)pyrimidineHCID 10825530HCID 10825530, compound

Product 1

HCID 250047055-amino-1-[5,6-diphenyl-2-(trifluoromethyl)pyrimidin-4-yl]-3-(methylthio)-N-phenyl-1H-pyrazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-hydrazino-5,6-diphenyl-2-(trifluoromethyl)pyrimidine (0.2 g, 0.63 mmol) in methanol (6 ml) was heated with 2-cyano-3,3-bis(methylthio)-N-phenylacrylamide (0.5 g, 1.89 mmol), overnight, at 60-65° C. The solid that separated out was filtered and washed with isopropyl alcohol (3 ml) to yield the required product. 1H-NMR (CDCl3) δ: 1.98 (s, 3H), 6.96-7.57 (m, 15H), 7.25-7.30 (2H, D2O exchangeable), 8.86 (br, 1H, D2O exchangeable); MS m/z: 547.1 (M++1).

Workup

  1. customThe solid that separated out
  2. filtrationwas filtered
  3. washwashed with isopropyl alcohol (3 ml)

Sources & evidence

ORD record
ord-ab444bdd2748425582efe5c1b0c3886f
Source dataset
uspto-grants-2014_09
Patent number
US08828999B2

Reaction notes

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